Visible-light-induced transition-metal-free defluorosilylation of α-trifluoromethylalkenes via hydrogen atom transfer of silanes

被引:16
|
作者
Xu, Wengang [1 ]
Xia, Congjian [2 ]
Shao, Qi [2 ]
Zhang, Qiao [2 ]
Liu, Mingrui [1 ]
Zhang, Hongwei [2 ]
Wu, Mingbo [1 ,2 ]
机构
[1] China Univ Petr China East, Coll New Energy, Qingdao 266580, Peoples R China
[2] China Univ Petr China East, Coll Chem & Chem Engn, State Key Lab Heavy Oil Proc, Qingdao 266580, Peoples R China
来源
ORGANIC CHEMISTRY FRONTIERS | 2022年 / 9卷 / 18期
基金
中国国家自然科学基金;
关键词
FUNCTIONALIZED GEM-DIFLUOROALKENES; C-F; DIFLUOROALLYLATION; DEFLUOROBORYLATION; ALKYLATION; GENERATION; RADICALS; ALKENES;
D O I
10.1039/d2qo00894g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A feasible and effective synthetic protocol for silyl gem-difluoroalkenes was reported. With the cooperation of sequential single electron transfer and hydrogen atom transfer processes catalyzed by organic photocatalysts (4-CzIPN) and (i-Pr)(3)SiSH, defluorosilylations of trifluoromethylalkenes occurred smoothly with aryl and alkyl silanes under visible light irradiation. Notably, the protocol features broad scope, transition metal-free conditions, utilization of green solvents, and validity for the late-stage functionalization of bioactive molecule derivatives.
引用
收藏
页码:4949 / 4954
页数:6
相关论文
共 50 条
  • [21] Construction of Benzocyclobutenes Enabled by Visible-Light-Induced Triplet Biradical Atom Transfer of Olefins
    Liu, Jiaxin
    Hao, Tonggang
    Qian, Ling
    Shi, Min
    Wei, Yin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (36)
  • [22] Cascade cyclization for the synthesis of indolo[2,1-α]isoquinoline derivatives via visible-light-induced halogen-atom-transfer (XAT) and hydrogen-atom-transfer (HAT)
    Ma, Na
    Guo, Lin
    Shen, Zheng-Jia
    Qi, Dan
    Yang, Chao
    Xia, Wujiong
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (08) : 1731 - 1737
  • [23] Pillared Metal-Organic Framework Initiating Intermolecular Atom-Transfer Radical Addition via Visible-Light-Induced Electron Transfer Activation of Haloalkanes
    Liu, Xin
    Guo, Zhifen
    Che, Yan
    Bai, Rong
    Chi, Yanhong
    Guo, Chunyi
    Xing, Hongzhu
    ACS APPLIED MATERIALS & INTERFACES, 2021, 13 (29) : 34114 - 34123
  • [24] Visible-Light-Induced Iron(III)-Catalyzed Synthesis of Unsymmetrical Bis(indolyl)methanes through Hydrogen Atom Transfer
    Mandal, Kush
    Rana, Gopal
    Nur, Asadujjaman
    Ghosh, Sourav
    Jana, Umasish
    SYNLETT, 2024, 35 (20) : 2525 - 2531
  • [25] Metal-free catalyst for the visible-light-induced photocatalytic synthesis of quinazolinones
    Wang, Rongzhou
    Liu, Shiyuan
    Li, Longfei
    Song, Ao
    Yu, Shengsheng
    Zhuo, Shuping
    Xing, Ling-Bao
    MOLECULAR CATALYSIS, 2021, 509
  • [26] Metal-free visible-light-induced borylative/silylative pyridylation of vinylarenes
    Zhou, Yiting
    Liu, Bin
    ORGANIC CHEMISTRY FRONTIERS, 2024, 12 (01): : 142 - 147
  • [27] Synthesis of sulfone-functionalized chroman-4-ones and chromans through visible-light-induced cascade radical cyclization under transition-metal-free conditions
    Mei, Yousheng
    Zhao, Lulu
    Liu, Qi
    Ruan, Shuchen
    Wang, Lei
    Li, Pinhua
    GREEN CHEMISTRY, 2020, 22 (07) : 2270 - 2278
  • [28] Preparation of block copolymers via metal-free visible-light-induced ATRP for the detection of lead ions
    Sun, Yue
    Li, Juan
    Zhao, Mengyuan
    Liu, Yutong
    Zhang, Jiameng
    Lv, Chengwei
    JOURNAL OF APPLIED POLYMER SCIENCE, 2018, 135 (07)
  • [29] Investigations on the 1,2-Hydrogen Atom Transfer Reactivity of Alkoxyl Radicals under Visible-Light-Induced Reaction Conditions
    Liu, Dan
    Zhang, Jing
    Chen, Yiyun
    SYNLETT, 2021, 32 (04) : 356 - 361
  • [30] Metal-free visible-light-induced phosphorylation of unactivated alkyl iodides with white phosphorus as the P-atom source
    Chen, Fushan
    Peng, Jialiang
    Ying, Yue
    Cao, Yinwei
    Xu, Pengxiang
    Tang, Guo
    Zhao, Yufen
    GREEN CHEMISTRY, 2023, 25 (17) : 6629 - 6634